1-Benz­yloxy-1H-benzotriazole

Jebas, S.R.; Selvarathy Grace, P.; Ravindran Durai Nayagam, B.; Schollmeyer, D.

doi:10.1107/S1600536812028395

Volume 68
Part 7
Page o2239
July 2012

Received 19 June 2012
Accepted 22 June 2012
Online 30 June 2012

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.003 Å
R = 0.054
wR = 0.163
Data-to-parameter ratio = 13.7
Details

1-Benzyloxy-1H-benzotriazole

Samuel Robinson Jebas,^a P. Selvarathy Grace,^b B. Ravindran Durai Nayagam ^b ^* and Dieter Schollmeyer ^c

^aDepartment of Physics, Sethupathy Government Arts College, Ramanathapuram 623 502, Tamilnadu, India,^bDepartment of Chemistry, Popes College, Sawyerpuram 628 251, Tamilnadu, India, and ^cInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: b_ravidurai@yahoo.com

In the title compound, C₁₃H₁₁N₃O, the dihedral angle between the benzotriazole ring system [maximum deviation = 0.027 (16) Å] and the benzene ring is 10.28 (9)°. The C-C-O-N bond adopts an anti conformation [torsion angle = -177.11 (16)°]. In the crystal, the molecules interact via weak C-H [pi] interactions and aromatic [pi] - [pi] stacking [centroid-to-centroid distance = 3.731 (12) Å].

Related literature

For a related structure and background to benzotriazoles, see: Selvarathy Grace et al. (2012).

Experimental

Crystal data

C₁₃H₁₁N₃O
M_r = 225.25
Orthorhombic, P b c a
a = 11.2417 (5) Å
b = 7.8381 (8) Å
c = 25.3933 (18) Å
V = 2237.5 (3) Å³
Z = 8
Cu K radiation
= 0.72 mm^-1
T = 193 K
0.51 × 0.45 × 0.13 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (CORINC; Wiehl & Schollmeyer, 1994) T_min = 0.84, T_max = 0.99
2125 measured reflections
2125 independent reflections
1867 reflections with I > 2(I)
R_int = 0.000
3 standard reflections every 60 min intensity decay: 3%

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.163
S = 1.12
2125 reflections
155 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12-C17 benzene ring.

D-HA	D-H	HA	DA	D-HA
C13-H13Cg1ⁱ	0.95	2.86	3.685 (2)	145
C16-H16Cg1ⁱⁱ	0.95	2.99	3.691 (3)	132
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Wiehl & Schollmeyer, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6865 ).

References

Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Selvarathy Grace, P., Jebas, S. R., Ravindran Durai Nayagam, B. & Schollmeyer, D. (2012). Acta Cryst. E68, o1132.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wiehl, L. & Schollmeyer, D. (1994). CORINC. University of Mainz, Germany.

organic compounds